Laboratoire de Glycochimie, des Antimicrobiens
et des Agroressources UMR 7378 CNRS

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Actualités et Publications

An air-stable lithiated cathode material based on a 1,4-benzenedisulfonate backbone for organic Li-ion batteries,

Lakraychi, A. E.; Deunf, E.; Fahsi, K.; Jimenez, P.; Bonnet, J. P.; Djedaini-Pilard, F.; Bécuwe, M.; Poizot, P.; Dolhem, F.

Journal of Materials Chemistry A 2018.

To meet current market demands as well as emerging environmental concerns there is a need to develop less polluting battery technologies. Organic electrode materials could offer the possibility of preparing electrode materials from naturally more abundant elements and eco-friendly processes coupled with simplified recycling management. However, the potential use of organic electrode materials for energy storage is still challenging and a lot of developments remain to be achieved. For instance, promoting high-energy Li-ion organic batteries inevitably requires the development of lithiated organic electrode materials which are able to be charged (delithiated) at a high enough potential (>3 V vs. Li+/Li0) – a challenging point rarely discussed in the literature. Here, we evaluate tetralithium 2,5-dihydroxy-1,4-benzenedisulfonate as an air-stable lithiated cathode material for the first time and its reversible Li+ electrochemical extraction. Quite interestingly, in comparison with the dicarboxylate counterpart, it was observed that the theoretical two-electron reaction is readily reached with this organic structure and at an average operating potential of 650 mV higher.

Synthesis of phosphorus analogs of TSAO-T,

Moura, M.; Josse, S.; Postel, D.

Tetrahedron 2018, 74, 4721-4727.

Phosphorus Analogs of TSAO bearing an oxaphospholene ring instead of an oxathiole dioxide ring at C-3′ position were prepared. Strategy developed previously on saccharidic moiety was used with introduction of an electron withdrawing α group neighboring the phosphorus atom. Biological evaluation on both HIV-1 and HCV showed that these compounds have no activity.

The influence of chloride and hydrogen sulfate anions in two polymerised ionic liquids based on the poly(1-(hydroxyethyl)-3-vinylimidazolium cation, synthesis, thermal and vibrational studies,

Chaker, Y.; Debdab, M.; Belarbi, E. H.; Ilikti, H.; Haddad, B.; Moumene, T.; Wadouachi, A.; Van Nhien, A. N.; Abassi, H. B.; Abbas, O.; Bresson, S.

Eur. Polym. J. 2018, 108, 138-149.

The chemical reaction of 2-chloroethanol with 1-vinylimidazol as precursor led to the corresponding compound 1-hydroxyethyl-3-vinylimidazolium chloride [EtOHVIM+] [Cl−]. In the next step, treatment of [EtOHVIM+][Cl−] with 2,2-azobisisobutyronitril (AIBN) afforded the poly1-(hydroxyethyl)-3-vinylimidazolium chloride (poly[EtOHVIM+][Cl−]), Finally, the reaction of (poly[EtOHVIM+][Cl−]) and sulfuric acid led to poly 1-(hydroxyethyl)-3-vinylimidazolium hydrogen sulfate (poly[EtOHVIM+][HSO4−]) by replacing the [Cl−] halide by an [HSO4−] anion. The structure of these compounds was identified by 1H NMR, 13C NMR as preliminary spectroscopic characterization. To obtain information on the structure and vibrational behavior in these compounds, vibrational spectroscopy measurements were investigated by Fourier Transform-Infrared-Attenuated Total Reflectance and Fourier Transform Raman spectroscopy in the spectral range 600–4000 cm−1 and 4000–500 cm−1, respectively. The Polymerization of IL gave rise to specific marks in the Raman and IR spectra and enhanced its vibrational property. Also, in order to understand the thermal stability in these compounds, the results concerning the melting point, glass transition and decomposition were determined by thermogravimetric analysis (TGA), differential thermal (DTG), and differential scanning calorimetry (DSC). The results indicated that the poly [EtOHVIM+][HSO4−] compound showed interesting thermal properties like high temperature of degradation and low temperature of glass transition compared to poly[EtOHVIM+][Cl−].

XRD and ATR/FTIR investigations of various montmorillonite clays modified by monocationic and dicationic imidazolium ionic liquids,

Ahmed, A.; Chaker, Y.; Belarbi, E. H.; Abbas, O.; Chotard, J. N.; Abassi, H. B.; Van Nhien, A. N.; El Hadri, M.; Bresson, S.

J. Mol. Struct. 2018, 1173, 653-664.

Three different montmorillonites (Mts) labeled K10, KSF and SWy-3 were analyzed by X-ray diffraction and ATR/FTIR spectroscopy. The XRD results enabled validation of the purification process of the studied clays. In the spectral regions 3800–2600 and 1800-1300 cm-1, the study of different intensity ratios of peaks assigned to the OH bending and stretching modes displayed the specific vibrational behavior of SWy-3 which is certainly influenced by a greater proportion of Na+ in its structure. Before analyzing the clays modified by ionic liquids, we characterized two imidazolium based ionic liquids (ILs) with anion I-: [EMIM+] [I−] monocationic ionic liquid and [M(CH₂) IM2+] [2I−] dicationic ionic liquid. The passage from [EMIM+] [I−] to [M(CH₂) IM2+] [2I−] reveals significant vibrational changes through various modes: ν(NH), rings ν(CC), rings ν(CN), ν(CH2(N)), ν(CH3(N)) in addition to anion interaction modes. When purified, these ionic liquids modify clays, the XRD analysis shows that the studied modified clays exhibited higher d-value increase with respect to the purified Mts, and the reflection peaks 2θ (°) of plane (001) were displaced towards lower values as a consequence of the ionic liquid intercalation process. ATR/FTIR spectra recorded in the spectral zone 4000-600 cm-1 indicated the appearance of new peaks and a significant intensity variation between clays in relation to the type of chosen ionic liquid. These vibrational changes are directly connected to the presence of ionic liquids in clays. XRD and ATR/FTIR investigations show a stronger effect of the [M(CH2) IM2+] [2I−] dicationic ionic liquid on the Mts than the monocationic ionic liquid and the SWy-3 Mt is more sensitive to monocationic and dicationic ionic liquids than K10 and KSF Mts.

Synthesis and Insecticidal Activities of Novel Solanidine Derivatives,

Beaulieu, R.; Grand, E.; Stasik, I.; Attoumbre, J.; Chesnais, Q.; Gobert, V.; Ameline, A.; Giordanengo, P.; Kovensky, J.

Pest Manag Sci 2018, 0.

Potato (Solanum tuberosum) is the fourth culture in the world and is widely used in the agri-food industries. They generate by-products where alpha-chaconine and alpha-solanine, the two major solanidine based glycoalkaloids of potato, are present. As secondary metabolites, they play an important role in the protecting system of potato and are involved in plant protection against insects. To add value to these by-products, we described herein new glycoalkaloids that could have phytosanitary properties. RESULTS: Solanidine, as a renewable source, was modified with an azido linker and coupled by Copper catalyzed alkyne azide cycloaddition (CuAAC) to alkynyl derivatives of the monosaccharides found in the natural potato glycoalkakoids: D-glucose, D-galactose and L-rhamnose. The efficacy of our compounds was evaluated on the potato aphid Macrosiphum euphorbiae. The synthetic compounds have stronger aphicidal properties against nymphs than unmodified solanidine. They also showed strong aphicidal activities on adults and a negative impact on fecundity. CONCLUSION: Our synthetic neoglycoalkaloids affected Macrosiphum euphorbiae survival at the nymphal stage as well as at the adult stage. Furthermore, they induced a decrease of fecundity. Our results show that chemical modifications of by-products may afford new sustainable compounds for crop and plant protection. This article is protected by copyright. All rights reserved.

Metal-free oxidative esterification of benzylated monosaccharides,

Camara, T.; Bil, A.; Chagnault, V.

Carbohydr. Res. 2018.

Methyl glyconates have been attracting considerable attention as intermediates for the preparation of aryl C-glycosides, polyphenolic products, aliphatic polyesters, SGLT2 inhibitors, antibiotics etc … In view of the interest in those compounds, we report herein our work on the synthesis of methyl glyconates using an oxidative esterification carried out by molecular iodine. This reaction is catalyzed by non-toxic K4Fe(CN)6 that releases a small amount of cyanide ion into the reaction mixture. Four benzylated carbohydrates which contain a hemiacetalic functional group have been tested successfully.

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